ORGANIC CHEMISTRY-PRINT COMPANION (LL)
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
4th Edition
ISBN: 9781119659594
Author: Klein
Publisher: WILEY
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Chapter 25, Problem 90IP
Interpretation Introduction

Interpretation:

When leucine is prepared via amidomalonate synthesis, the by-product isobutylene is also formed and its mechanism needs to be drawn.

Concept introduction:

Amidomalonate synthesis is a process in which a halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 90IP

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

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Chapter 25 Solutions

ORGANIC CHEMISTRY-PRINT COMPANION (LL)

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